


Joke's On You

by DarthFucamus



Category: The Jester (MakeDo)
Genre: Anal Fingering, Condoms, F/M, Halloween, Halloween Costumes, Masks, Public Blow Jobs, Semi-Public Sex, Vaginal Sex, the mask stays on
Language: English
Status: Completed
Published: 2018-07-08
Updated: 2018-07-08
Packaged: 2019-06-07 08:32:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,946
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15215201
Author URL: https://archiveofourown.org/users/DarthFucamus/pseuds/DarthFucamus
Summary: Anonymous said:“You should totally write a Jester/OC thing when you want to!”Anonymous said:“if u feel like it, could u write a jester/oc one shot pls. the masked guy from that horror short”Penelope gets off work late Halloween night and encounters a strange, sorta creepy masked man who charms the pants off of her. Sexual mischief abounds!





	Joke's On You

**Author's Note:**

  * Inspired by [Remember To Smile](https://archiveofourown.org/works/15215096) by [FancyLadySnackCakes](https://archiveofourown.org/users/FancyLadySnackCakes/pseuds/FancyLadySnackCakes). 



> I was just as charmed by this guy as you, anon(s), and since my pal FancyLadySnackCakes got the same request, we both thought it’d be fun for each of us to write a short fic about him in our own styles and share them at the same time :) 
> 
> Look up "The Jester" by MakeDo Entertainment on Youtube if you're curious about him, they've made a couple of good little horror shorts about this character of theirs (the second one is especially enjoyable)

Penelope escaped from work around 8:30 PM even though the grooming salon was meant to be closed by 8:00. It was Halloween night and that meant last-minute walk-ins in addition to the full appointments on the book.

Everyone wanted the cute halloween-inspired dog bows and bandanas, and seasonal ‘after bath spritz,’ and as her old manager used to say before selling the business to her, turning down money was like taking it directly out of the register. She didn’t think the pumpkin spice dog perfume smell would ever totally leave her stylist smock, but it could have been worse.

But she had a party to get to, anyway. She used the shower in the employee bathroom to wash the smell of dog off of her and changed into her costume.

She did her makeup, feeling much refreshed. After donning her oversized hoodie that came to her mid-thigh, all that was visible were her stocking-clad legs and sparkly ballet flats.

New Market street flowed with pedestrians and partygoers. Halloween was kind of a big deal here, but so was every other holiday in the wealthy town. Rich people loved their masquerades and cocktail parties, but Penelope had her own plans to look forward to.

Main street was cool and breezy and a few costumed revelers were out and about, no doubt on their way to some party or other, just like her. She waved goodnight to the pharmacist across the street, an older man in a pirate hat, as he locked up his drug store.

She closed up Penelope’s Pooches, humming a song from a Halloween kid’s movie, thinking about the party, hoping that what she was wearing was good enough. No doubt some of the other people would have expensive custom-made stuff to show off, but It didn’t matter, she looked fucking great in it, and at least her costume bore some resemblance to what it was actually supposed to be.

She got out her phone to tell the girls she would be on her way shortly and made her way to the parking spots on the side of the building.

A stranger was standing by her scooter, inspecting her helmet. He looked like he was in costume, with a cartoonishly large black top hat and a tangerine-orange men’s suit.

“Uhm, excuse me?” she said to the man’s back. He put the helmet down on the seat and turned to face her with a faint jingle like hidden bells or chain links. She had no idea who this guy was, he’d hidden his face behind a devious grinning mask.

“Happy Halloween,” she said, offering him a smile that told him she’d give him the benefit of the doubt, for now. He removed his hat, revealing short, clipped light-brown hair, and dipped into a low bow.

She offered him a little nod and he returned the top hat to his head, casting shadow over the evil, molded-plastic smile.

“Nice costume, dude,” she said, pointing at the getup with the hand holding the crinkling plastic bag. The suit was a little dirty in places, as were his white polyester gloves, but maybe his Halloween celebration had started early. “What are you supposed to be? A clown?”

An evil clown, maybe, she thought, finding it hard to keep her eyes off the bottomless pits where his should’ve been.

She examined him from his black leather dress shoes to the top of his oversized formal hat. He was already tall, but the headpiece easily put him over seven feet.

He held up his pointer finger with the tinkle of clinking metal, as to say ‘wait for this,’ and removed the top hat. Holding it upside down by the brim, he reached inside. Penelope glanced around to see if anyone else had noticed him, but only saw a few scattered costumed revelers, caught up in their own enjoyment and destinations. Main Street had quickly emptied out as the last of the shops closed, and she was alone with this guy. He was funny, at least.

He sank his arm past the elbow before he stopped at the ‘bottom,’ a clever illusion, and Penelope offered a polite sound of awe. He rummaged around, really worked his shoulder into it as though sorting through an impossibly large amount of junk to find something. She could even hear something like heavy objects being shoved about, and whatever he was wearing that chimed like bells was jangling chaotically with his movements. She smirked, and stood back, crossing her arms.

There was no harm in letting him try to impress her, especially as  _ tall _ as he was, and attractive... at least from what she could see. Not to mention, the effort he was putting into playing his part had to count for something. And it was hard, at times, to process that the sinister face was a false one; shadows shifted in the streetlight from above, deepening the hard-cut planes of the jester’s face.

He found what he was looking for, it seemed, expressing his satisfaction in body language too extravagant to be anything but funny, and withdrew his arm. His face brightened jovially under the light as his white glove emerged from the depths. It gripped the curved head of a black wooden cane. This, too, he pulled out of his seemingly bottomless top hat.

She couldn’t see any joints on the staff of the cane that might make it collapsible. Now she really was impressed. She clapped as he slapped the hat back onto his head and dipped into a quick bow.

“Cool tricks! So, you’re a magician or something? You kind of look like the Joker. The scary cartoon one, not the hot Heath Ledger one,” she said, and then realizing that might be perceived as an insult, added, “not that you’re not hot or anything, I can’t really tell with the mask and all. But it’s a nice look.”

He offered an inquisitive head tilt in response to her babbling and her cheeks flooded with embarrassed warmth as she realized that no, she actually  _ did _ think he was hot, even with the mask on.

“You ahhh going to a party?” she asked the stranger, eyeing his tallness and the way he stood with his back straight and his gloved hands perched on the end of his hook cane. She liked his bearing. Self-confident without taking himself, or anything it seemed, too seriously. The mask, which she decided more resembled a devilish imitation of a court jester than a clown, didn’t hurt that perception.

He did a slow, jaunty, jingling little dance, motioning with both hands, cane tucked, at the world around them, which she interpreted as a indication of ‘going with the flow.’

“True, sometimes it’s fun to be spontaneous, isn’t it?” she asked, finding herself moving imperceptibly nearer to him. “There’s nothing to do on this side of town, though, sorry to say. I have a party to go to myself, actually.”

She had the momentary urge to invite him, but dismissed it. She had no idea who this guy was, and the last thing she needed was a hanger-on cramping her plans. With his cane tucked under an arm, he tugged at the lapels of his tangerine formal suit pointedly, then nodded at her with a sweeping, questioning gesture. Penelope looked down at her nondescript hoodie and her sparkly ballet flats.

“Oh, I have a costume. Sort of,” she said with a secretive smile. “Speaking of, I need to get going, man. It was nice meeting you, though, thanks for the laughs!”

She sidestepped to get around him to her scooter, but he moved to match, blocking her with his cane held horizontal on either end. He motioned for her to wait before she could get even a word out, and she huffed with mild impatience.

The girls would be expecting her soon. She was itching to cut loose; there would be more than a few stares she wanted to land on her outfit.

Her eyes darted around her periphery to verify that the street was as empty as she thought it might be. Everything closed up early on the older end of Market street, it was just the two of them, but she wasn’t worried, yet.

Until he pulled a condom out of an inside pocket.

“Whoah, tiger,” she said, stepping back. Without a word he tore open the foil packet and discarded it for the latex disc. He gave her a look as he unrolled it over his gloved index and middle finger, ribbed for her pleasure. He wiggled his fingers seductively.

Heat flooded her cheeks and she covered a giggle with her hand as he continued to stretch the thin latex over his entire gloved fist. The nerve of this guy!

“Where do you think  _ that’s _ going?” she asked, smirking despite how daunting the sight was. She checked her phone, and when she looked up, he’d removed the condom from his hand and turned partially away. She couldn’t see anything, but she heard him blow up the condom like a balloon. She craned her neck, trying to be subtle and catch a glimpse of his face, but he kept his face well out of sight.

Penelope was really tittering, now as he peered back, fully masked, over his shoulder, hands manipulating the latex balloon, twisting it and shaping it into a balloon dick. He turned around and offered it to her. Penelope accepted it with a wry smirk. She had to admire his persistence and tenacity.

“Thanks. Think you can make two? I plan to have a very busy night,” she said with a snicker.

He took off his hat and fanned himself and gave her a look of pure, unchanging mischief. Her cheeks pinked.

“Do you want to see my costume?” she asked, feeling adventurous. “Maybe you can tell me what you think?”

He nodded fast. She glanced around them to make sure no one would see, and unzipped her hoodie. She pulled it open, giggling and biting her lip.

He did a Chaplin-esque stumble back, bells tinkling somewhere on his person, holding onto his hat. He dipped forward, bracing on his cane like a cartoon wolf looking at little red riding hood. She wasn’t the sexy red riding hood character from the cartoons, but she  _ was _ sexy. Her powder-blue princess costume was little more than a micro-dress with poofy taffeta to fill out the skirt, and a low, sweetheart neckline that offered her bosoms to their full effect. To complete the look, she pulled a plastic tiara out of her purse and placed it atop her head.

The jester clutched his heart and fanned his face and Penelope couldn’t help but feel gratified at his exaggerated reaction. She gave him another look over, and couldn’t help but notice how he stood now, creepy mask a little hunched, and closer to her. It made her pulse pound in her ears.

“Look, I don’t normally do this, but…” she started, then waved the dick-balloon. “If you do have another one of these, you wanna go somewhere more private? My friends can wait.”

He squared his shoulders, then gestured questioningly around them, and the way the shadows pulled into deep, diabolical lines made the fine hairs on her arms stand on end.

She bit her lip and looked around, heart pounding for her reckless impulse. Her eyes landed on the sign a little ways down the street, marking the local park. There were plenty of shadowy places where a couple of consenting folks could take their business without being seen.

He followed her eyes, then looked back to her, and offered his arm.

\-----

The old park wasn’t that big, it was maybe an acre of mowed grass and spaced out trees in the middle of upper class suburbia, but close enough to the main street that she could still hear distant revelers, perhaps even people who would recognize her if they were to see her face.

But she wasn’t Penelope the posh pet stylist right now. She was a sexy princess and he was the rakish court jester, pushing her onto a roman-style concrete park bench, intent on ravishing her.

Or something like that. She wasn’t sure it was a cohesive fantasy scenario, but she was getting into the spirit of things, mewling flimsy objections as she tugged him down by his lapels, clinking some unseen bells or metal chain as she did. It was so sordid, and the thought that someone might see them only made it more exciting and urgent.

To his credit, he’d remained completely silent from the first moment he ‘introduced’ himself, but Penelope could hear him breathing behind the plastic molded mirth when she all but dragged his body on top of hers. It was just enough feedback to excite her further.

“You have thirty seconds to show me why I’m here with you instead of at my party,” she said to him, grinning. The downward tilt of his face was especially ominous. He cupped a hand over her ear, then pulled on something. Fabric rustled and a brightly colored handkerchief began to emerge from what was clearly meant to be her ear, and she sighed.

“More magic tricks? Seriously, man-”

He stuffed the wadded handkerchief into her open mouth and she grunted in protest before he shoved her little skirts up to her waist, showing her garter straps and the ridiculous snap-crotch underwear she was wearing.

He couldn’t see her grinning, but she was, as she let her legs fall open on either side of the park bench. He grabbed her under her knees and pushed, straddling the bench and sliding forward until her legs rested on top of his thighs.

She offered a plaintive whimper pleased by his boldness when he undid the snaps on her open crotch. By the cool autumn air hitting her there, she knew her arousal was obvious. Truth be told she’d wanted to fuck him the second he pulled out that condom. With a flourish, a second condom made an appearance out of nowhere. She just hoped he planned to use this one for its intended purpose.

She watched him demurely as he pulled out a long, blood-flushed cock with his dirty white glove and rolled the orange condom over it with a smooth wrist-motion. Her mouth hung open at the lovely, flush-tipped length of it before the entire shaft was encased in a thin layer of pumpkin-orange rubber.

He watched her as he guided it between her legs, and she scooted her hips closer to him until she felt the hard, latex-clad knob that made her think of a plastic whiffle bat.

There was no sleight of hand, no magic or tricks, he just pushed it past the entrance, glided through tight, wet flesh on the slick of her arousal. He stretched her so nicely that she moaned into the wadded handkerchief, grabbing onto his gloved hands where they held her thighs. He drove his dick in with a good, enthusiastic thrust and she gasped, startled and appreciative of his lack of preamble.

He jutted his hips, smacking into her ass with every core-pounding strike as she filled the wadded makeshift gag with her drool and stuttered cries. Over the wet smacking of bare hips against bare ass cheeks, a musical ringing accompanied his every move. The angle was nice, though not as deep as she would have liked, and tilting her hips to receive him only helped some.

She didn’t know how he did it, but the next thing she knew, he was twisting her body to the side without pulling out, flipping her into a doggystyle position with her hands braced on the bench. Grabbing her hips tight and adjusting her, he sank himself into her deep, enough that it hit her cervix and she gasped and spread her legs for better balance.

The touch of one of his hands disappeared, and no sooner was she curious about its whereabouts than the wooden hook of his cane slid around her neck. Her nerves spiked and she groaned. He found a rhythm, stroked her butt cheek as he rammed into her, and his unseen balls smacked her vulva with gleeful enthusiasm.

He railed her from behind with the cane hooked around her neck. There was a sharp pop as he spanked her ass with his dirty white glove. Penelope didn’t restrain her moans, and the cane was little more than a pleasant diversion than an actual attempt to choke her. If it weren’t for the handkerchief, she knew her noises might have drawn attention. She was less concerned with being seen in a fairly public place than she was about the stability of the concrete park bench, which wobbled every time the jester rammed into her with the sound of a myriad of tiny bells.

Her elbows got weak, her stomach tightened, and her nails bit into the concrete as the wild heat surged. Her arms were shaky, unsteady, but she still tried to go for her clit one-handed.

Off balance, a good thrust pushed her forward and into the bushes next to the bench, and he came down with her and kept fucking her as she sputtered with leaves in her mouth and whimpered.

“Yes! Yes! Oh fuck! Oh  _ fuck! _ ” she wailed, though it was unintelligible around her gag, as twigs and branches poked into her cheeks and chest. Helplessly and gleefully she took the punishing thrusts even as they pushed her deeper into the manicured foliage of the park bush, because every single one ramped up the sweet burning in her belly.

She heard a rubber snap, and then a slick, latex-clad fingertip probed between her jiggling ass cheeks and found a sensitive, puckered second hole. Startled, she gasped, and with hot red cheeks, she bobbed back against his body, crinkling foliage and snapping twigs, willing to let him to do whatever he wanted to her.

He slipped his digit into her aided by whatever lube he’d used, a thumb, she thought, and gently wiggled it inside her ass while he fucked her pussy. Something about the discomfort of the second penetration sent a flood of heat between her thighs where it gathered heavily, and she tried not to clench too tight, but it was hard.

She could barely stifle her enthusiastic wails, and the gag only did so much, as he fucked her into the bushes. The force of it made her slide onto the grassy ground beside the bench, and she lay with her ass up and her hot cheek against the cool grass, a princess in a state of joyful disgrace.

His hat fell off and rolled away but he didn’t stop, doggedly persistent, perhaps driven by the helpless noises she was making, driven to escalate her vocal ecstasy to a new crescendo. He pulled his thumb out, slid it back in past the joint, and Penelope almost didn’t get her hand under her and on her clit in time to influence the building pleasure, but the first couple of swipes was all she needed to careen into a dirty, noisy orgasm.

The man behind her stayed planted through her contractions, humping a few more times. After, he patted her on the cheek affectionately with his cane hand, removed his thumb from her ass, and collapsed on her back, panting hard.

She spat out the handkerchief and started to giggle, but it turned into a moan when the jester gave another playful thrust with his hard cock.

“You can’t be done already,” she said between panting breaths, craning to look back at him.He peeled off the condom he’d used to fuck her ass with and slingshotted it into a trash can with perfect aim.

He made an exaggerated gesture like wiping sweat from the forehead of his mask. His dick was still hard when he pulled it out of her, though. She made a small noise of disappointment, but when he offered a hand, she let him help her to her feet. He brushed the leaves off of her, and the dirt scuffed on her cheek and knees, then he guided her to sit on the bench. He bent over and picked up her tiara from the ground and placed it gently on her head.

It was all very gentlemanly until he stood before her with his hard cock at face level and began peeling off the condom.

“Oh I see,” she said, smirking. “You think I talk too much, huh?”

He gave a comical shrug before taking his dick in hand and wiggling it provocatively. It was no worse than what she’d planned to do tonight, anyway, and so much more exciting in the middle of a municipal park at night than she thought it would be.

He’d earned it, she had to be honest, and her shaky knees and warm, comfortable feeling made her glad to have a seat. If he was headed to the same party like she was convinced by now, there was no harm in a little pre-gaming.

She opened her mouth and leaned forward, guiding his cock between her open lips. She had been expecting the bitter taste of spermicide, but instead tasted... pumpkin spice. A seasonal flavored condom, she thought with a smile. She tongued the underside of his knob with a little more enjoyment.

Penelope looked up because she knew some guys liked that, but found herself lost in the playful horror of the jester’s grinning mask. The eyes were endless boreholes in a shade somehow darker than their surroundings, even in the shadowy park. She bobbed her head forward, squeezing with her lips, feeling the heartbeat in the veiny shaft as the jester’s eyes swallowed her and his overstretched maw smiled at her.

It was both frightening, for how her brain played tricks on her that it wasn’t a mask but his skin, and indescribably alluring after he’d fucked her so rudely.

She was getting so into blowing him, it was like she was feeding off the unsteady swaying of his upper body and head, and the ragged breaths coming from behind the creepy mask, that she didn’t notice him bringing the hook of the cane around the back of her neck until the inside of the curve pulled against it.

He trapped her there with it and began humping her face. She held onto the back of his thighs, ready to tell him to stop if it got to be too much. His cock was long enough that it would have gagged her had she not been practicing at home. She let show the full extent of her progress, dragging her tongue and sucking all of the pumpkin spice flavor from his cock skin as she invited him into her throat.

He anchored her there and pumped her straining jaw, breathing harshly but still voicelessly.

A white glove cupped her jaw and cheek to feel them working around his fat erection, and she looked up and now saw eyes glittering eerily through the eye holes of his mask, and they almost startled her. With a sharp thrust that nearly choked her, he grunted and the fat ridge underneath surged and flooded her throat with warm jizz.

Penelope tasted both sweet and salty as she swallowed the pulsing spurts. She squeezed his leg and he unhooked his cane from the back of her neck, interpreting her nonverbal cue to perfection.

He dragged his hand up the side of her face and into her hair almost sweetly as he withdrew his weeping, twitching cock. Penelope took some breaths and wiped her mouth, a little confused because his cum tasted kind of like… caramel. Like he’d been eating nothing candy for a few days.

“Fuck  _ me,  _ that’s sweet,” she gasped, wiping her mouth on her forearm as he carefully tucked his dick back into his fly. “You’re fun, but maybe you should lay off the sugar?”

He dipped into a genuflecting bow and offered her his elbow before rising. She slid her hand around it, taking his gallantry with good humor, and laughed when he brought her hand to his ‘mouth’ for a polite kiss.

WIth a showy gesture, he ‘conjured’ a piece of wrapped candy from nothing, and offered it to her. At this point she wasn’t so surprised to see the trick, even if she wasn’t sure how he was doing it.

“Gee, thanks,” she said, accepting it even though she wasn’t sure if she should be insulted or appreciative. His cum might have tasted a little sweet but it was still cum, so she accepted the slightly-crushed candy and started untwisting the crinkly plastic.

“Hey, so what are you doing later?” she asked, popping the bonbon into her mouth.

The guy looked left, looked right, shrugged, then motioned to her. Penelope giggled around her mouthful of sugarbomb, almost losing a splash of caramel-drool in the process.

“I’d be alright with that,” she said, looking down at her sparkly flats before peering up at him demurely. “But I’m going to a party, so you’d have to come with. You can be my plus one, if you want. I should warn you, it’s a Halloween lingerie party, if you couldn’t tell. Kind of dirty, but, like, classy too. Uh, kinda like you?” she felt her face turn ruddy with the admission, but didn’t take it back.

He did a impish, little dance, tinkling like windchimes. A clear ‘yes,’ though he looked uncomfortably like a marionette jerking on strings when paired with the masked veneer of intense gaiety. She decided she didn’t care if he was weird, she kind of just wanted to be around him so she could see what he did next.

“Got any more tricks? Besides that thumb thing, I mean,” she said, snorting as he wiggled his fingers atop his cane and an almost imperceptible tremor passed over him. He gave her a couple of floppy nods.

The jester gave his cane a good shake and collapsed into a large piece of black fabric, and Penelope gasped with genuine awe and clapped. It was a large piece of fabric, too, almost like a black silk cape, and she had no idea how it could have been concealed on his person or in the cane somehow. She didn’t have a thing for magicians or anything, but she kind of wanted to blow him again.

Holding the cloth up behind him, he gestured her closer to him with a dirty, flashy white glove, and then invited her underneath it with his distorted sculpted grimace.

A pair of bottomless, eyeless holes were the last thing she saw before he threw the cape around them both with a swirl and a jingle and a swish of fabric. Silk slid over her face, wrapped over her back, forced her closer to the man’s body. He smelled like apples and caramel popcorn and it made her mouth water even with the candy he’d given her still gumming up her teeth.

She got the same stomach lurch as though she were standing at the edge of a steep drop and was tempted, for just a second, to jump.

Her mind told her she was falling and she lurched against him off-balance, and into long, gripping arms. She caught her breath, and got a good whiff of whatever delicious scent he was wearing that made him smell like fresh pastry.

“God, save it for the party,” a woman said. Penelope opened her clenched eyes and peeked. She was still holding onto the jester, who just stood there like a post until she gathered her wits. They were standing in the street, and the woman who’d spoken to her was sashaying her way up the long drive to the house in a “bunny” costume that was little more than a lacy corset with a white tail and long fuzzy ears.

Bass-heavy funk music was bleeding down to the street and multicolored lights flashed in the front windows of the brick colonial revival mcmansion. She heard laughter and more activity outside from the back of the house. They’d arrived, somehow, right where she’d wanted to go.

“Holy fuck,” she said, turning in place as though she might see the mirrors or trap doors behind the magic trick if she gawked long enough. Taxis with more partygoers were arriving and walking around them to get inside and Penelope couldn’t figure it out, so she gave up trying.

“Let me know if you ever make it big and need an assistant,” she said, turning to look at him, half-serious. He reached into his suit jacket, jangling faintly, and when his dirty white glove emerged, he held a flimsy plastic mask, silvery grey with a single elastic string.

He offered this to her with uncharacteristic gravity, and something about the angle of his face and the faint pulses of colored light coming from the house behind her, added a murky undertone of otherworldliness to his wicked expression.

She accepted it, knowing it for the proposal, and perhaps even the unspoken contract, that it represented. When she moved to put it on, he helped her. She corrected her tiara and the jester offered feedback in the form of a patter of muffled clapping and a wolf whistle.

Penelope decided that she didn’t really care what anyone else thought of her princess costume, her new friend certainly appreciated it.

As he escorted her up the driveway behind a fit Tarzan and “slutty” Jane, Penelope knew that as long as she stuck around this guy, who or  _ whatever _ he was, she was bound to have a Halloween she wouldn’t soon forget.

**Author's Note:**

> Hope you like my take, and be sure to check out Fancyladysnackcakes story as well!


End file.
